


Something Awesome

by Word_Smith_94



Category: Supernatural
Genre: Appreciative Dean Winchester, Boys in Skirts, Confident Castiel, M/M, Praise Kink, Public Sex, self exploration
Language: English
Status: Completed
Published: 2021-02-19
Updated: 2021-02-19
Packaged: 2021-03-16 03:08:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,486
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29569401
Author URL: https://archiveofourown.org/users/Word_Smith_94/pseuds/Word_Smith_94
Summary: Castiel has always wanted to be pretty, and, to him, a skirt screams pretty. Tonight, the first time he's been confident enough to wear one, he's heading to the club to see what people think. And maybe, just maybe, he'll find someone who finds him really pretty.
Relationships: Castiel/Dean Winchester
Comments: 5
Kudos: 82





	Something Awesome

Castiel stares at the clothes on his bed, hands shaking. He wants them, so much, but now that he can, he freezes. Can he bring himself to follow through now that he has a chance? 

A dog next door barks, the apartment walls too thin to stop the noise. It snaps Castiel back into action, and he reaches out to feel the soft texture of the skirt. Thin pink fabric falls in pleats that will let it flare out when Castiel twirls his hips. The spaghetti strapped white tank top with an inch of lace around the bottom hem adds a touch of pretty.

Clearly designed for a woman, not a man like him. Castiel knows he’s a man, but he wants to feel pretty, wants someone to tell him that he’s pretty, and it’s hard to be pretty in men’s clothes.

College is about finding yourself, so it’s now or never.

Starting with a shower, Castiel preps for a night at a club. He shaves his body hair, all of it, and washes every inch of himself. Once done, he blow dries his hair and uses a little gel to make it look messy but not too messy.

Naked, Castiel walks over to his dresser for lube and a plug. Nothing massive, nothing crazy, just enough to keep him on edge, keep him focused on his body all night. Who needs a partner for foreplay?

A little bit of lube smeared on the plug, and Castiel props his foot on his bedframe to slide it in with ease. He puts his foot back down and wiggles a bit to make sure the plug sits right. His cock starts to thicken a bit, responding to the stimulation.

Next, Castiel pulls out his new jock strap, running his fingers over the lace, anxious to feel it on his skin. He steps into the jock, shivering as the lace brushes up against his freshly shaved legs. The pouch cups his dick just right, and the lace covers his hips and the top of his ass cheeks. He spins to check his ass in the mirror, pleased with the way the lace frames his ass.

Ass ready and picture perfect, Castiel heads back to his bed and pulls on the tank top. His fingers grab at the skirt, hesitating for a moment, but Castiel pushes through the nerves to pick up the skirt and puts it on, elastic band sitting on his waist.

Castiel checks himself in the mirror again, so happy with what he sees. He has a runner’s build, lean enough the clothes sit on his frame well, but there’s still no denying he’s a man. That’s what he wants though, to be a man that someone might find pretty.

He grabs a denim jacket, slips his phone, wallet, and keys inside then puts on his favorite purple Converse. The door automatically locks behind him, then Castiel locks the deadbolt and heads downstairs to wait for the Uber he scheduled earlier.

His ride arrives soon after he arrives outside the gates. Castiel slips into the back and settles in as the driver pulls away from the curb. “Looking good. You got a lucky someone waiting for you at the club?” the driver asks.

Castiel blushes, shifting around, trying to find a position that doesn’t shove the plug into his prostate. It takes a moment to process the driver’s question. “No, no one special. Just looking for a fun time. Meeting my friends there.” While they haven’t planned anything, there’s a really good chance that Gabe will show up at the club on a Friday night.

She smiles at him in the rearview mirror. “Have fun. You look great, and I’m sure you’ll have a good time. Love your outfit.”

Castiel beams at her, so glad to hear that. He knows his outfit looks good, but external confirmation makes him that much more confident.

At the club, Castiel eyes the line, trying to see if he recognizes anyone. He hasn’t been to a club in a while, so he’s not expecting much. Near the front, he sees Gabe, his cousin, and jumps up to say hey.

Gabe’s eyes grow wide and he throws his arms open for a hug. “Well, if it isn’t my little cousin Cassie! What got you out of the house?”

“I got a new outfit,” Castiel tells him, twirling in place to show off his shirt without going too high to show his ass. Not yet at least. “Wanted to show it off.” He feels like a little kid again, waiting for family approval.

Gabe wraps him in a tight hug, holding him in place for a moment before stepping back. “You look great, and I’m glad you’re happy.” They smile at each other before Gabe gestures to he two men with him. “Sam and Dean. Guys, meet my cousin Cassie.”

Sam nods at him with a small smile. “Nice to meet you.”

“Nice to meet you too. How’d you meet this sucker?” Castiel asks, pointing over at Gabe. His cousin sucks in an ‘offended’ breath, and Sam smirks.

“We had to work together on a project for a business class,” Sam explains, “and we figured out we like he same clubs, so we get together when we’re heading out. Dean’s my brother, and he got dragged along with us.”

Castiel smiles at Dean who doesn’t say anything, just looks him up and down. He starts to second guess his outfit. “This your kind of club?” Loud and Proud isn’t for everyone.

The question seems to snap Dean out of his thoughts, and the man looks up with a smirk on his face. Castiel sucks in a breath when he sees his face. Bright green eyes, nice stubble, plush lips, and a bone structure that he can’t describe but wants to trace and get to know.

“Never been here before, but if everyone there looks like you,” Dean says, eyes running up and down his body, “tonight’s going to be fantastic.”

Dean sounds like a player, really good with lines, but the look in his eyes says he actually means it, at least a little bit. Castiel blushes and returns the look. Loose jeans, tight tee shirt, leather jacket, he doesn’t really look dressed for the club, but Sam did say they made Dean come with them. “Should be fun.”

Sam and Gabe chat together as they wait in line, and Castiel stands next to Dean, watching him out of the corner of his eye, trying not to be too obvious. Dean smirks at him, so clearly, he failed.

“Gabe didn’t expect you. Clubs not your thing?” Dean asks before things can get too awkward.

Castiel shrugs, not quite sure how to explain. “I don’t hate clubs, but I don’t always feel comfortable there. I don’t like guy’s club wear.” And he hasn’t had the courage for a skirt before.

Dean turns them so they’re face to face, hands on his arms as Dean looks him up and down again. “Well, if this is your compromise, looking good.” He spins Castiel around, his skirt flaring out, and Castiel tries to show off his ass just a little.

“Really?” Gabe, the driver, both good opinions, but a hot guy who he’d love to grind on in the club? The best opinion to hear.

Dean pulls him close when he completes the spin, forcing Castiel to look up to meet his eyes. “Really. And I’ll buy you a drink if you let me see more of what’s underneath.”

Arousal rushes through him as Castiel pictures Dean behind him, one big hand on his hip, another cupping his dick under his skirt. Then he’d bend Castiel over something, flip up his skirt, and see just how good his ass looks in lace. His ass clenches at the image, jostling the plug into brushing his prostate. He can’t hold back a low moan, one that makes Dean’s eye widen before he smirks at Castiel.

“Any drink you want, pretty boy, any drink you want.” Their bodies sway into each other, bumping chests for a moment. Part of his brain feels good that Dean knows for sure he isn’t a girl no matter what he’s wearing. “But not too many, because you need to know what you’re saying yes to, and I want you to remember everything.”

God, sexy and interested in consent. How did Castiel get so lucky before even getting inside? Castiel smiles at Dean, not really sure what else to say right now. He runs his hands over Dean’s chest, trying to get an idea of what his shirt hides.

Broad chest, firm muscles. Castiel likes what he finds. He has a thing for defined pecs and that v line, especially with a happy trail, and Castiel has a feeling Dean has everything he likes.

Someone snapping breaks their focus on each other, and Castiel turns to see Gabe watching them with a look on his face. The move makes him lean into Dean’s chest, feel all those lovely muscles at once. “You want to pay and get in, or do you want to stare at each other all night?”

“We’re coming,” Castiel tells Gabe as Dean pulls out his wallet. He slaps Castiel’s hands down when he tries to grab his own, paying for both of them together. Dean keeps an arm around Castiel as they make their way into the club, and Castiel doesn’t bother hiding his smile, taking advantage to grope his pecs as they walk.

Dean doesn’t say anything, doesn’t push him away, just keeps smirking and keeps Castiel close to him.

Inside, there isn’t enough space for them side by side, so Castiel ends up in front of Dean. He makes sure to twitch his hips side to side a little extra to keep Dean’s focus on his ass. He can feel his eyes on him just like he wants.

“I’ll go get drinks,” Gabe shouts over the music while gesturing at the bar. They nod, Sam leading the way through the crowd, his height the ultimate tool. Castiel notices several people looking at him, and he stands a little taller. He looks good, damn it.

They find a booth opposite the DJ booth, pretty far from the bar too, and Castiel ends up sandwiched between the two brothers. Sam gives him space, but Dean crowds him, arm around his shoulder and practically pulling him into his lap.

“You gonna pee on him too?” Sam asks, looking between them. Castiel blushes while staying right where he is, not bothered at all.

“No need,” Dean growls, looking out at the crowd as if he’ll stare down anyone who even thinks about looking as Castiel. “I saw him first, so I get first chance to impress him.”

Pretty sure Dean managed that when he called Castiel pretty, but he won’t say no to more effort. “Dancing impresses me a lot,” Castiel says, looking up at Dean from under his lashes. He skipped makeup today, not wanting to push it too far. Next time, he’s definitely wearing mascara at a minimum.

“Drinks first,” Gabe announces, appearing out of the crowd, his height making him blend in. “I want a chance to talk to my cousin before you steal him for sex.”

“Gabe!” Castiel hisses, grabbing his drink and taking a sip. He coughs when the alcohol goes down the wrong way, the mint of the mojito just adding to the burn. Dean rubs his back through the coughing fit. “I’m not having sex in the bathroom. That’s your thing.”

Flipping him off, Gabe grabs his beer and sits next to Sam. “You have a quickie in a bathroom once, and they _never_ let you live it down.” He waves his hands and gestures large, but they ignore his craziness.

“Tell me more,” Dean says, drinking his beer. “You got fully naked with someone in a club bathroom?”

Gabe shakes his head at him. “Nope. Just my dick out, but my partner was totally naked, tits and balls out. Got almost to the end when Cassie here walked in, almost ruined my orgasm.”

“Sorry for screaming at seeing my cousin going at it with a naked stranger in a bathroom over the sink.” Castiel shakes his head while twisting enough to put his legs over Dean’s lap to lean his head against his shoulder. It feels super easy, being with him, and he’s gonna soak in everything he can.

“You’ve never gotten wild in public?” Dean asks him, looking down at him while his hand rubs up and down his side.

Castiel takes another sip to stall a bit. “I haven’t had full penetrative sex in public. Hand jobs only.” Doesn’t matter that his favorite fantasy involves sex on a dance floor. Side benefit to skirts: easy access.

Dean tips Castiel’s head back so their eyes meet, studying him. “You ever think about it? Or is it a no go?” The loud music forces Dean to put his mouth right next to Castiel’s ear so Gabe can’t hear and chime in, and Castiel shivers as Dean’s breath brushes over his skin.

Although he can’t remember the last time he did a one night stand, Dean tempts Castiel like no one else. “Depends,” Castiel tells him, deciding in the moment. “Can my partner put on a condom while on the dance floor?”

A long moment makes Castiel hesitate, but then Dean grins at him, full of promises. “You want it, I’ll make it happen for you, pretty boy. Any chance to keep you tonight.”

Castiel doesn’t want to play it safe tonight. He tosses the rest of his drink back and pushes at Dean so he can leave the booth, dropping his jacket on the seat. Standing up, he fixes his skirt before leaning over to tell Dean, “I’ve even got a plug in. It was just for me, but apparently I planned ahead.” He smirks at the blank look on Dean’s face and heads out to dance.

Bodies press up against his as Castiel tosses his hands in the air and lets the music move through him, the occasional brushes against other bodies adding to the experience. It doesn’t take long to start moving and find a girl to dance with. She raises an eyebrow at his outfit but lets him back up to her chest and grind together.

They fit well together, her hips cradling his ass thanks to her heels, and they keep their hands to themselves. Castiel gets sweaty fast, even without his jacket, and he knows sweat will turn his tank top translucent in no time.

His nipple piercings will stand out even more with a damp shirt.

Moving with the music, Castiel manages to turn them enough they face his table. He watches Dean watch him, a hand hidden under the table. If he wants to jack off, fine, but he better not cum before he fucks Castiel. Castiel wants that dick in his ass.

Deciding to tease, wanting that fuck sooner rather than later, Castiel start teasing his nipples through his tank top. The sensations feel amazing, his cock swelling in his jock. Anyone who couldn’t tell before now can definitely see he’s not a woman. Sure, the crowd blocks part of the view, but Dean will see soon enough.

Something Castiel does makes Dean crack, and he pushes away from the table to stalk through the crowd to Castiel. People move out of his way without looking, Dean’s determination and focus enough to give him space. He grabs Castiel’s arm and pulls him away from the woman, glaring at her and even growling a bit.

As Castiel spins around, his back to Dean’s chest, he sees the woman smirking at him while finding another dance partner. Given how close Dean holds him, the possessive hand spread across his lower stomach, the tight grip on his hip, Castiel understands. He’s smirking too.

“Mine, Cas,” Dean growls right in his ear. “Told you I get first dibs on impressing you.”

Castiel reaches up and behind him to wrap an arm around Dean’s neck. “You did, coming to get me and show me how much you want me.” Possessiveness and jealousy are hot, within reason. In the club, super hot. “You can feel just how much.”

He wants someone to fondle him on the dance floor before fucking him. Dean obliges, the hand on his stomach slipping under his skirt and right into his jock, no coy touches over top. Fisting Castiel’s cock, Dean starts jacking him off as much as he can while trapped by Castiel’s skirt.

Castiel moans at the feelings moving through him, hips jerking into Dean’s grip for more friction. He should care that anyone could see, but he doesn’t give a shit. If he could get a hand between them, he’d return the favor.

“Your voice kills me,” Dean tells him, hand still moving along his cock. “Want to have you in my space where I can take you apart and hear all those little noises, pretty boy.” Castiel moans again at the picture of them in a bed, wants to see all of Dean, but can’t find the words to tell him that he wants the same. “You gonna cum for me tonight, Cassie, then gonna let me do it all over again?”

He can’t take the words anymore. Castiel spins in Dean’s arms, his hand sliding around to his ass, so he can kiss Dean. Not the most coordinated kiss ever, but their lips move against each other until Dean takes over, pushing his tongue inside Castiel’s mouth.

Dean’s fingers find the plug in Castiel’s ass a moment later, and he starts pushing it in, each time brushing Castiel’s prostate but no serious pressure. It teases and plays but doesn’t give him what he really wants. Pulling back from the kiss, Dean smirks at Castiel who looks up at him full of arousal and not much more. He can’t think through it.

“You didn’t lie about the plug.” Dean pushes the plug deepest yet, pushing Castiel harder into his chest. “And I can feel lace. You dressed up all pretty for yourself?”

Castiel manages to nod, pinned between Dean’s hard chest and the plug in his ass. “Wanted to be pretty even if people didn’t care.” Although he really hoped someone would appreciate it. “Glad you think I’m pretty.”

“Pretty,” Dean agrees, “and fucking sexy when you grind up against me.” Dean follows up by grinding his cock against Castiel’s stomach, and he can tell Dean will fill his ass with a serious stretch.

“Sexy enough to fuck me?” Castiel begs, practically desperate now. It started back when he put the plug in his ass, and every interaction with Dean has only increased his arousal.

“Gotta get closer to the middle,” Dean tells him, “make it harder for them to throw us out.” Keeping them chest to chest, his fingers playing with the plug again as Dean moves them deeper into the crowd.

As they reach the center, bodies brush up against his arms and back, no space for them to move without contact. Castiel notices a few people registering where Dean’s hand sits, and they give him knowing looks but don’t say anything, just continue dancing with their own partners.

Dean moves his mouth down to Castiel’s ear as they stop moving and start grinding together again in an approximation of dancing. “Condom in my back pocket. Put it on me?”

Castiel slips a hand into his back pocket, distracted by the firm muscles under his fingers. He gropes Dean’s ass, pulling a few moans from him, but the feel of foil draws his focus back. Pulling out the condom, Castiel uses his teeth to rip it open, holding the foil in place for the moment.

Now he has to figure out how to undo Dean’ pants without losing the condom. He pouts, confused, not sure how to handle this, especially with their crotches pressed into each other and people bumping him. Dean chuckles and grabs the condom to slip it into his front pocket.

He puts his hands on Castiel’s hips, and now Castiel aims his pout at Dean, especially when he puts a little space between them. “Gotta take me out first.”

Right, that would help. Castiel manages to undo the buttons of Dean’s fly, pushing his pants open but not down. No boxers or briefs, just warm, hard cock in his hands. Castiel plays with him a bit, jacking Dean a few times and smearing precum along his length. Dean hisses in his ear as his hips buck, getting some precum on Castiel’s skirt.

That’d better wash out.

Ignoring the urge to get on his knees to lick up some precum, Castiel fumbles for the condom again, the wrapper drifting to the floor as he focuses on pinching the tip and rolling it down Dean’s cock. Dean stays still just long enough to be useful before spinning Castiel around so they’re back to front again.

Cold air caresses Castiel’s ass when Dean flips up his skirt, and he shivers knowing anyone who looks over will see his ass. Dean moans and palms his ass, kneading his ass even as he pulls Castiel back, Dean’s cock between his legs and hitting his balls.

Whining with need, Castiel tries to push back into Dean, as much as he can with his ass in his crotch, trying to tell him to fuck him. Dean just squeezes his ass, playing with him, before pushing Castiel away.

He whines again, the only noise he can make right now, not wanting distance between him and Dean. Something tugs at his rim, and Castiel relaxes, realizing Dean wants to remove the plug. When it pops out, Dean puts it somewhere, then he shoves his cock in his ass.

Holy fuck, the burn. Dean’s long, pushing past his prostate and providing a heady dose of pleasure to counter the burn of the stretch. Not too thick, thankfully, the lube from the plug and the condom enough for Castiel.

Dean pulls Castiel back upright, his skirt falling back down to cover them up. The move shifts Dean’s cock in his ass to press even harder against his prostate. Castiel moans and grinds down into it, wrapping an arm around Dean’s neck again, something to anchor him.

“Fuck me, Dean,” Castiel orders, grinding and moving on his cock as much as he can. “Doesn’t need to be hard, just keep it deep.”

“Want me to fill you up?” Dean asks while rolling and thrusting his hips to build a little friction between them. If it wasn’t for the high of doing this on a dance floor, it might not be enough, but with eyes on them, all the build up starting when he got dressed, Castiel won’t last long.

“Fill me up, make me cum,” Castiel orders. “Play with my nipples, Dean, do it.”

Dean obeys, pinching and tugging, the added sensation amazing, especially when Dean reaches around to fist his cock too. “Gonna play your body until you’re cumming so hard your ass squeezes my cock and makes me cum.”

Fuck, that sounds amazing, him cumming triggering Dean’s orgasm, and Castiel swears he’ll make it happen no matter what. He can’t do much, not with them posed like this, but he can do something.

Castiel twists enough that he can pull Dean’s head down enough for them to kiss. More a press of lips than an actual kiss, but they moan into it, and Dean moves his hips a little faster. The music picks up the pace as well, pushing them to move even faster.

Eventually Castiel can’t handle it anymore, the pressure on his prostate and the hand on his cock too much. He cums all over Dean’s hand and his jock with a shout muffled by Dean’s lips. Dean keeps jacking him through it, keeps thrusting his hips even as Castiel shudders in his arms.

As he cums, Castiel’s ass clenches down on Dean’s cock, reminding him just how deep it goes. He does his best to keep clenching, trying to push Dean over the edge, and it doesn’t take long. Dean groans long and low, body tensing behind Castiel as he cums.

“Fucking hell, pretty boy,” he mutters as the aftershocks wear off. “Gonna make me see heaven with that ass of yours.”

“Next time, we’ll do it in bed,” Castiel promises, not sure how it’ll happen but knowing he’s not going to let Dean get away without promising a next time.

“For fucking sure.” They sway together, still connected, until it starts to get a little awkward. Dean takes care of the condom, tucking it away somewhere before grabbing Castiel’s hips and pulling them close together. “Dance with me?”

“Definitely.” Castiel needs a moment to calm down again, his body still wound up. The wet jock sucks, but he can’t figure out how to get it off without flashing everyone.

They move together, comfortable together, and Dean’s hand somehow manages to come to rest cupping Castiel’s cock. It makes the cooling cum even more uncomfortable, but he loves it too.

But Dean picks up on something bugging Castiel. “What’s wrong, pretty?”

“Wet spot.”

Dean chuckles and slips his hands under Castiel’s skirt, toying with the waistband of the jock. “I’ll pull it off, step up when I tap your ankle.”

Not quite sure about this, Castiel jumps when Dean pulls his jock down in a quick tug. He remembers to lift his feet, and Dean’s back behind him in a moment, jock probably shoved in a pocket. “Something to remember me by.”

“You’re unforgettable, baby, even without a memento,” Dean tells him. Castiel blushes at the compliment, glad Dean can’t see him blush.

They keep dancing, moving together for hours, not even stopping for drinks. Castiel wants to keep touching Dean just in case this turns out to be a one-time thing. Amazing things don’t normally happen to Castiel, not when he’s just an average person.

But they have to leave eventually, Sam tall enough to gesture over the crowd for Dean to leave. Castiel came via Uber, but Dean drove Sam and Gabe. As they move off the dance floor, Dean manages to wrap an arm around Castiel’s waist, giving him hope.

“You two have fun out there?” Gabe wiggles his eyebrows saying he knows exactly what they got up to. Castiel hides his face in Dean’s chest as he flips off Gabe. “You taking Cassie home? He came via Uber.”

Dean looks down at Castiel, and Castiel nods, accepting a ride. And maybe, if he’s lucky, next time might be tomorrow morning. Based on the look Dean gives him as they head out, the hand practically attached to his hip, Castiel’s feeling pretty good about his chances.

Maybe he can get something awesome.


End file.
